CHEBI:68006 - lehualide F

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ChEBI Name lehualide F
ChEBI ID CHEBI:68006
Definition A member of the class of 2-pyranones that is 2H-pyran-2-one substituted by a methoxy group at position 3, a hydroxy group at position 4, a methyl group at position 5 and a (2E)-3-methyl-9-phenylnon-2-en-1-yl group at position 6. Isolated from the marine sponge of the genus Plakortis, it exhibits cytotoxicity against human promyeloid leukemic HL-60 cells.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C23H30O4
Net Charge 0
Average Mass 370.48190
Monoisotopic Mass 370.21441
InChI InChI=1S/C23H30O4/c1-17(11-7-4-5-8-12-19-13-9-6-10-14-19)15-16-20-18(2)21(24)22(26-3)23(25)27-20/h6,9-10,13-15,24H,4-5,7-8,11-12,16H2,1-3H3/b17-15+
InChIKey RLHYLTRNTUTEBU-BMRADRMJSA-N
SMILES COc1c(O)c(C)c(C\C=C(/C)CCCCCCc2ccccc2)oc1=O
Metabolite of Species Details
Plakortis (NCBI:txid86044) Methanolic extract of frozen sample See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing lehualide F (CHEBI:68006) has role antineoplastic agent (CHEBI:35610)
lehualide F (CHEBI:68006) has role metabolite (CHEBI:25212)
lehualide F (CHEBI:68006) is a 2-pyranones (CHEBI:75885)
lehualide F (CHEBI:68006) is a ether (CHEBI:25698)
lehualide F (CHEBI:68006) is a polyketide (CHEBI:26188)
IUPAC Name
4-hydroxy-3-methoxy-5-methyl-6-[(2E)-3-methyl-9-phenylnon-2-en-1-yl]-2H-pyran-2-one
Registry Number Type Source
21452356 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21351759 PubMed citation Europe PMC
Last Modified
17 March 2014